Madonna. Two decades later, and she is still as fearless as ever. We sat down with the boy toy turned yummy mommy to see how her life.. has changed.

[ dissolve to Matt at sit-down interview with Madonna in another studio ]

Matt Lauer: You look wonderful. You seem great.

Madonna: I am great. I have a wonderful family. and I’ve never been happier.

Matt Lauer: Madonna, you’ve been famous for so long. You’re 44 years old now. How does it feel to be so old?

Madonna: Sometimes bad.. sometimes sad. Always old.

Matt Lauer: What is a day with the old Madonna like? What is her typical schedule?

Madonna: My day is like everyone else’s. Two hours of yoga.. an hour of intense Kabalah study.. followed by underwater pilates.. tea and scones.. a three-hour argument with Guy Ritchie in the street.. my children’s pilates.. and.. I usually end the day by having a three-way with Sting and Trudy Styles.

[ dissolve back to Matt Laurer standing alone in the studio next to giant monitor ]

Matt Lauer: Madonna. The old broad seemed as feisty as ever. And I was doing pretty well without Katie. I spoke to Madonna about her career choices. And here’s what the 50-year old pop icon had to say.

[ dissolve back to Matt at the sit-down interview with Madonna in another studio ]

Matt Lauer: You’re 58 years old. Anything you regret in your life?

Madonna: I don’t like to use the word “regret”. I feel that one can never regret their art. They can only desperately wish that they had not.. shaved their art.. taken pictures of their art.. and put their art in a book.

Matt Lauer: So, you have no regrets?

Madonna: No.

Matt Lauer: You don’t regret “Dick Tracy”?

Madonna: Nope.

Matt Lauer: “Shanghai Surprise”?

Madonna: Never saw it.

Matt Lauer: Dennis Rodman.

Madonna: He led the league in rebounding.

Matt Lauer: You’re telling me you don’t regret.. “Swept Away”?

Madonna: [ sighs ] “Swept Away” was the kind of movie that was.. not supposed to be good.. and, if people can’t understand that.. well, then, I just don’t know..! [ laughs ] [ dissolve back to Matt Laurer standing alone in the studio next to giant monitor ]

Matt Lauer: Madonna. The 62-year old who never stops re-inventing herself. She took a moment to show me.. how she’s learning to play the guitar.

[ dissolve to Madonna holding steady to an acoustic guitar ]

Madonna: [ strumming her guitar off-key ] It’s really important to get out of your “comfort zone”. I’ve made a lot of progress.

[ dissolve back to Matt Laurer standing alone in the studio next to giant monitor ]

Matt Lauer: Madonna. 70 years young. Despite her decision to pull her controversial video, “American Life”, the album debuted at #1. When she performed her in-store concert.. “Dateline”.. was there.

[ dissolve back to Madonna performing her in-store concert at Tower Records ]

Madonna: [ surprised ] Oh.. I don’t know.. I haven’t sung that one in a while! Is that still a song any more? [ laughs, as two-man band plays behind her ] I’ll try it.. [ singing ] “Like a vi-i-i-irgi-i-i-innn.. touched for the very first-” [ changes pitches of her voice ] Gotta find my key.. [ samples different pitches until she’s back on track ] Like a.. like a.. like a.. like a-” There it is! “Like a vir-r-r-r..” That’s not it.. [ begins singing with a deep voice, then stops ] You guys suck!

[ dissolve back to Matt Laurer standing alone in the studio next to giant monitor ]

Matt Lauer: There you have it. Madonna. Sexy. Fearless. 80 years old, with a vagina closing in on a hundred. I’m Matt Lauer, and.. yes.. I’m going to keep my hair like this for a while. And, no.. I don’t know when it’s going to grow back. And, yes.. my wife likes it. And, no.. Katie is not as nice in person. Good night.

Author: Don Roy King

Don Roy King is directing his fourteenth season of Saturday Night Live. That work has earned him nine Emmys and thirteen nominations. Additionally, he has been nominated for thirteen DGA Awards and won in 2014, 2016, 2017, 2018 and 2019. Mr. King is also the creative director of Broadway Worldwide which brings theatrical events to theaters. The company has produced Smokey Joe’s Café; Putting It Together with Carol Burnett; Jekyll & Hyde; and Memphis, all directed by Mr. King. He completed the screen capture of Broadway's Romeo & Juliet in 2013. - LinkedIn View all posts by Don Roy King